The Cute Girl With The Red Glasses
by AlienfromNorth
Summary: Leonora Knight hates gossip. But being the daughter of a rich businessman and living on the Upper East Side of The Big Apple makes it a bit hard to escape. Especially when she catches the eyes of several Upper East sider boys.. [re-uploading the story, rated T for now]
1. I

**A/N: Hi everyone! This is my first Gossip Girl fanfic, it will be playing out the tv show and I have not read the books. Slight AU, everyone attends the same school which is St. Jude's. Hope you all enjoy. Please R &R. **

**Also a warning! My OC will have mental health issues and OCD. If that is in any way a trigger for you to read, turn away from this. Though she not in any way suicidal, she is being bullied.**

 **~X~**

New York drove Leonora insane. The people, the buildings, the noise. Everything added up to one nice, permanent headache. Today that particular headache was in a form of a party that her father had promised that it would be a quick in and out situation. They had been there for over an hour. Leo didn't even know who organised this gathering, but her father had said that it was good to socialize with others that were the same age as her. Looking around the room, she felt as if didn't belong on the upper east side of New York.

But she was, in fact, the daughter to the one and only Tyler Knight. One of the world's wealthiest men alive. He owned the Knight Group, an insurance company that worked globally with other wealthy people and their insurance, from anything like a dog to a house or family members. Because of this, she went wherever he went. And for now that would be the big apple.

"So Nate, started to think about college yet?" A man in the circle that Leo and her father stood in asked. Nate Archibald was a guy in Leo's school. They did not have many classes together since most of Leo's schedule consisted of AP classes.

"Well actually I'm a Dartmouth man" His father stated with confidence. Leo wanted to roll her eyes, as always, the father had the last word about his son's education. Like Nate was just a doll to be presented to the world. 'Look, my son does this, went there and can work with this' and another man would say 'This is my daughter, she does this and is very pretty. She is also prepared to drop everything in her life for your son'.

"Yes, dad's always spoken highly of Dartmouth, but I would like to check out west, maybe USC or USLA" Nate said, his eyes glaring daggers at his father. Yet also seeking approval in some way.

"His mother wouldn't have it, Dartmouth is far away enough for her" _And that is final._ Leo thought and sipped on her drink.

"What about your daughter Tyler?" The same man turned to her father as if Leo wouldn't be able to open her own mouth to speak.

"Oh I am very proud of her, 4.0 average and I get emails everyday from Ivy League schools trying to take her away from me. But I want her to finish at the normal pace you know, life is no rush" Tyler stated as he drank his whiskey. The other men around him nodded.

"So do you have any particular school in mind?" The man asked Leo who looked like a deer caught by headlights on a freeway.

"Umm.. I have so many to pick from, but Harvard sounds amazing. I also got a letter from the university of Oxford in England, and since my older brothers are in charge of father's company division in London I think it is an option to consider" Leo smiled. She hadn't stammered once, nor fidget with her hands. She even looked him in the eyes, but then looked at her father instead for comfort.

"Just brilliant, you have done good raising her Tyler" Another man stated and clapped her father on the back. The other's joined in on the praise. Nate's father just stood there quietly, looking over at Leo then to his own son.

"Excuse me Captain, Nate can I borrow you?" The one and only Blair Waldorf asked. Smiling like a little angel. With Nate gone, Leo moved out of the group and towards the table with the different foods and desserts. As she placed down her glass, she picked up a small bowl of strawberries and started to eat them one by one. Trying discreetly to move closer to the exit. She would explain to her father later that evening that she felt sick and went home, and that she forgot to text him because of her light-headed state.

"Well look what we have here, the black sheep trying to escape the herd" A voice exclaimed behind her. Leo turned around to face Chuck Bass. Her arch-nemesis.

"Chuck, just please let me go" She stated, he would rat her out in front of her father's friends. Which would then turn into gossip. Leonora Knight dreaded gossip.

"Why is that Leonora? Are you not having fun?" He chuckled in his husky voice, Leo shuddered and turned her head towards her father's direction. He hadn't noticed her yet.

"No, and I want to go home" She said and put her bowl down on a nearby table. She looked Chuck in the eyes as if to say 'I dare you'.

"But you know that I will cause a scene if you go.. and right now we are having so much fun" He threatened. He had bullied Leo since first year of high school when she had spilled her water all over him in the middle of the cafeteria. Everyone had laughed at him. And it wasn't so much spilling the water as it was throwing it at him. Since he touched her without a heads-up.

"Will you ever let it go Chuck? You know that I couldn't help it" Ah, and then it was the fact that Chuck knew about her mental health issues and also the obsessive compulsive disorder. The price you gotta pay for an IQ over 130.

"Who knows, all I know is that toying with you is fun. See you around, Leonora?" He said, then stepped away to go and talk to some of Blair's minions. Leo sighed and hugged herself. She felt like a coward, because all she wanted to do was to get out of the poisonous party.

"Are you alright?" Leo opened her eyes to find Nate standing there. She furrowed her eyebrows. He never talked to her. Or acknowledged her existence for that matter.

"Yeah, I'm.. I'm fine" She said and turned away from him.

"What did Chuck say to you, he can be a real ass you know" Nate stated and looked straight at her. She felt naked, why was he staring?

"He.. He just says stuff sometimes, it's fine really" Leo tried to convince him, but since she wouldn't meet his gaze he knew it was more than what she tried to play it off as.

"I will talk to him-"

"No! Please, don't. Nate, I'm fine. I just really need some air" Leo said and walked out the front door. To hell with Chuck Bass.

Leo didn't know, but Nate looked at her until he couldn't spot her anymore down the hallway. He had just gotten over Serena and he was still together with Blair. But it was something about Leo that made him smile.

 **~X~**

 **Knight Residence, Upper East Side**

 **Monday**

"Ah there she is! My little genius is a junior now" Chris exclaimed. He had been Leo's nanny ever since she was a toddler, and he was a great one too. Chris Andrews had been a high positioned agent at one of New York's best model agencies before he decided that he needed a break from all the glamour and made a fabulous exist to live a 'simple life'. He apparently knew Tyler from a couple of parties back in the day and when an old friend called in to baby sit, just over the weekend, Chris gladly accepted. He then fell in love with little Leo so much that when Tyler said he was looking for a nanny he took the position with pride.

"You are way too excited" Leo sighed and adjusted her skirt. Chris had probably hemmed it without her knowing it, again.

"Stop pulling at it! You look gorgeous honey" Chris said and fixed her tie so that it was straight. Leo had braided her black hair into boxer braids, since it was way to unruly and wild to just keep down. While eating a quick and amazing breakfast, all regards to Chris's wonderful cooking, she did the crossword puzzle in the New York Times. Chris hummed a tune from the radio while going over a fashion magazine, at the same time packing Leo's lunch, just to look up at the clock on the wall and gasp.

"Leo you better get ready to run dear, you will be late for school" Chris sighed and gave her the lunch boxes. Leo almost choked on her orange juice and gathered up her things.

"Bye Chris, I will be home as usual. Love you!" Leo shouted as she sprinted towards the elevator.

"Love you too honey!"

 **~X~**

 **St. Jude's**

"For the first assignment of this semester you will work in a group of two, you will choose a mythology or non-abrahamic religion and do a presentation together in front of the whole class. The things you need to have in your presentation are questions like, what was the effect by the mythology on society of the time? Are there traces of those mythologies still in modern society? Etc. You will have two weeks to complete it and it will have a great effect of your grade" The teacher of AP history wrote every word he said on the board. Leo sat by the the window, but was nose deep in writing down notes to remember for later.

The teacher of the class was very strict and old fashioned. He believed in old fashioned good work and gave every half-assed assignment an automatic F after reading the first paragraph.

"And the pairs are.. Adam B and Greg, Juliette and Lorelei G.. Klara and Chuck" The teacher wrote to lists next to the assignment. Leo did not care about this part. She just hoped that whoever was partners up with her would not let her do all of her work alone.

"Leonora and Nathaniel" Leo stopped writing and looked up, _you've gotta be kidding with me!_ Leo thought and looked around the classroom, halfway through she met Nate's eyes. What does the universe have planned. That boy seemed to show up everywhere since that stupid party.

 **~X~**

 **Lunch**

"Leonora! Hey!" She looked up from her greek mythology book and spotted Blair Waldorf sitting a couple of steps to her right. First she looked around to see who she really meant, then she realised she had called her out by name.

"Hello?" Leo said, barely audible.

"Here, take this" Blair said and gave her a golden letter. Raising her eyebrow she opened it and read the invitation.

"Why would you…"

"Just take it okay? It is on Saturday"

"But-" Leo would've argued against it. Then spotted Serena beside Blair. They had been fighting passive aggressively and were now having a glaring contest.

"Fine.. thank you for the invite" Leo sighed and stood up from the steps. She really needed to get away from the drama. Still feeling eyes on her back, she picked up the pace. When she finally reached the school grounds again she opened the letter and read the whole thing. It all seemed off, she had never been invited to any party before. She didn't even care about these parties anyway. She turned the invite and saw none other than Chuck Bass's neat handwriting.

 _Hope you save me a dance princess_

 _XO you know who_

"Why doesn't he just leave me alone" Leo muttered and threw the letter into her leather bag.

 **~X~**

 **Central Park**

 **Nate and Chuck POV**

Walking with Chuck made Nathaniel relax and tense up at the same time. How could that be? Well he felt like he could tell Chuck anything, but he had to be careful about his words of choice.

"This is some good stuff" Chuck commented while blowing smoke out of his mouth.

"Yeah I'm gonna need it, Blair's mom is at the countryhouse" Nate exclaimed, but didn't seem happy about that at all.

"Yeah, well then maybe I should swipe some of my dad's viagra.. or my mom's paxil?" Chuck looked at his best friend.

"Nathaniel you are about to have sex with your girlfriend, you act like you are headed to your execution" He added, now frowning to get Nate to fuss up.

"Nah man I'm good" Nate just wanted him to drop the matter, but he was damn persistent.

"Talk to Chuck buddy, you and Blair have been dating since forever and all of the sudden there's a problem?"

"There's no problem, it is just... do you ever feel like our whole lives have been planned out for us? Like we are just gonna end up like our parents" Nate murmured, feeling a slight weight disappearing from his shoulders.

"That's a dark thought" Chuck said while Nate scoffed. Then he remembered the party last weekend.

"By the way, what's with you and Leo?" Nate asked, taking the joint from Chuck's hand.

"Leo?"

"Leonora Knight, you know who I mean I saw you talking to her at that party"

"Oh.. you mean the pretty princess? Nothing, we were just talking. She is coming to that party Blair is hosting this saturday" Chuck laughed a bit and rolled his eyes. But Nate knew something wrong was going to happened.

"Really? She doesn't seem like the partying type to me" Nate said and took another hit.

"Look, smoke up and seal the deal with Blair. Because you are entitled to tap that ass" Chuck stated and took back the joint before going away from his friend, who had a now terrible feeling in his gut.


	2. II

**A/N: This is still episode one, will go onto episode two. My story will not be episode to episode and be a rather go with the flow (a.k.a the tv-shows storyline).**

 **OBS! Rewritten May - 2019**

 **Thank you all for reading! XOXO**

 **~X~**

Leo looked around the party. Feeling insecure in her navy blue dress and high heels. She had never walked around in those kind of shoes before, being a ballerina flats kind of girl. But she had to admit that they made her feel different, in a good way. She sighed, why was she even there? Maybe some part of her, the tiny bit that actually enjoyed being one of Manhattan's elite, had pushed her way through the anxiety ridden mind of Leo and in doing so taken the most extroverted decision she had ever done as of yet. Maybe some part of her, wherever it revised within her, wanted to actually try. At least once.

At yet the whole aura of the venue made her want to disappear, fighting her pure hatred of touching strangers, and also trying to focus with the loud music blaring from the speakers.

"It doesn't make sense" Leo muttered to herself. Looking around the room once more. She had no idea of what to do now. Her logical side listed off what one would might do at parties, and some appealed to her more than others. Maybe getting one of those fruity drinks was something she should do.

"So the pretty princess arrives.. Kinda hot how you listens to my every command" Chuck Bass appeared in front of her, the lights and sounds had distracted her long enough for him to sneak up on her and now looked her up and down shamelessly. He liked the dress, adored the heels. She looked ten times more grown up as the other girls around him. Her inky hair was up in a ponytail that she had flattened. She even wore a bit of makeup, all casual except for her lips, which were a dark purple color.

Even though he despised the innocent girl before him. All he wanted to do was to claim her and make her less angelic. Kiss those dark lips, then her jaw and neck. Chuck would bet that hearing Leonora Knight moan his name would be the most erotic sound on the planet. She was too good for this place on earth, and she needed to be grounded. Clip her wings, so to speak.

"I am here Bass. Now tell me why" Leo rolled her eyes. His stares made her skin crawl.

"Oh so the kitty got claws. The night is only getting better" He said and stepped closer.

"Tell. Me. Why" She said again, avoiding his black, sinful eyes.

"Do you know what I don't get princess? How can a girl like you. With so many secrets. Not have a single trace of her online. Nothing on social media, nothing on Gossip Girl. How can you avoid it" Chuck asked.

"Simple, don't draw attention to yourself" She stated, her voice naturally callus and calculating. She pushed her glasses up the bridge of her nose.

"Hmm.. let's go up to the roof" He said and took a hold of her wrist. Pulling her with him through the crowd and up the staircase. Grabbing a few glasses and a bottle on his way. To anyone looking at them it would be the normal case of Chuck Bass going in for another conquest. But Leo was actually starting to get nervous. She didn't like when people touched her, but his hold on her wrist was strong. When they reached the roof he let her go, standing out there with the New York skyline as their view was kind of romantic in Chuck's mind.

"So what now" Leo said, biting her lip very hard as to not move towards the door.

"Calm down princess, we are in no rush" He put the bottle and glasses down on the ground and stepped closer to her. Even though she didn't like it she put her hands on his chest to push him away.

"N-no, I may be a coward for letting you step all over me for three years. But now you have gone too far Chuck" Leo said and started to go for the door. But he once again grabbed her arm, pushing her up against the nearby wall. Trapping her in between him and the bricks, Leo officially started to panic.

"Chuck, stop, I know you hate me but... goddammit! get away from me!" She struggled against his grip on her. Chuck realised what he was doing and let her arms go, instead, he placed his hands on either side of her head. He realised that Leo was panicking beneath him, and something inside of him felt disgusted of his actions.

"What are you doing?" Leo practically whispered. Chuck was staring at her, trying to figure out something. Why was it so hard to do exactly what he wanted with her, like he had done with many girls before. Why was this puny, innocent, naive girl somehow affecting him and his decision making.

"GET AWAY FROM HER!" Suddenly Chuck was thrown away from her, making her gasp for air. Leo hadn't realised that she had started to cry, nor when she did. But when she looked at the guy who saved her, she smiled. She also smiled because he had hit Chuck right in the face, which made the new guy her hero.

"Thank you" Leo said gratefully. Serena was there and wrapped her coat around her. Instinctively she pulled the expensive clothing closer to her.

"Dan, let's get out of here.. Now" Serena said and moved quickly with Leo towards the exit. While inside the party they met up with a girl that looked a lot like Dan, and Leo guessed that she was his sister. He gave her a short scolding, but together they moved away from everything.

"Hey are you alright?" Nate asked, seeing Leo with red puffy eyes, hair disheveled and bruises all over her neck and arms.

"No.. you can tell Chuck Bass and Blair Waldorf that I hope they rot in hell" Leo growled and gave Serena her coat back as she went out of the party. Nate, seeing red that his friend and girlfriend caused someone physical harm went out of the party as well.

"Leo! Leo, wait!" He shouted after her, seeing her walk down the street with her heels and clutch in hand.

"What? Are you gonna hurt me to!" She shouted. Frustrated that she thought she actually would enjoy the night. She thought that Chuck just wanted to talk, to clear the air between them. Then she would've tasted some fruity drink, maybe danced or mingled. Maybe actually start a conversation with a cute guy. But no. None of that happened.

"No! Never.. Just, let me get you a cab. Let me walk you home, you can't walk several blocks alone" He sighed as she finally stopped to listen to him. Leo didn't say anything, she was just so tired and nodded. It took a while, as it was a saturday and most cabs would be full this time of night. But Nate manages when he pulls out a 50 dollar bill and waves it in the air. Together they get into the cab in silence. The only word said are Leo's address, which happened to be relatively close to Nate's.

"I am not gonna apologize for them. But I am sorry that you had to go through that at all" Nate said, trying to break the glacier of ice in between them.

"Thanks" Leo said and smiled. It was a small smile, but Nate's chest grew warm just by that simple gesture.

"I umm.. We should get together soon. For the presentation in history class" He suggested, glancing over her and smiled when he saw a faint blush cover her cheeks.

"Yeah, whenever and wherever you'd like I guess" She muttered, still looking at her hands, and not him.

"Hey did you know, that the average woman uses her height in lipstick every five years?" Leo stated with a giggle. Wanting the break the silence in the cab too.

"No way" Nate laughed, Leo was a wonderful human being. Knowing random facts like that, being actually kind towards others and even being a bit introverted made him want to get to know her more.

"It is true! And.. did you know that the total number of steps in the eiffel tower is 1665" Leo said and giggled some more. Nate laughed again and shook his head.

"So.. you know facts. How smart are you?" Nate asked and looked Leo in the eye. She smiled at him.

"Well, let's just say that I'm smart" She stated with confidence, Leo didn't know why but she wanted to open up to him. But suddenly it was easy to share things. They arrived at Leo's building and Nate moved quickly to open up the door for her like a proper gentleman. He helped her inside and to her elevator, even going so far as to push the button for the penthouse.

"Goodnight Nate" Leo said and waved at him, a silent gesture as a thank you. She then stepped further into the elevator before the doors closed. Going back out on the street and into the cab once more, Nate couldn't help but think two things. _I'm gonna kill Chuck_ and _God, I think I like her._

Then his phone buzzed. _Shit._

 **Spotted: The pretty princess getting hot and heavy with C, then left with another, taken, man. Does the Queen B know what her precious king is doing behind her back?**

 **You know you love me, XOXO Gossip Girl**

 **~X~**

 **Knight Residence, Upper East Side**

 **Morning After**

"Good morning everybody" Tyler Knight sighed as he made his way to the dinner table, they were going to have a light breakfast before attending The Bass Brunch. Which of course the Knight family had been invited too.

"Good morning dad" Leo muttered as she didn't move her eyes away from 'The count of Monte Cristo'. It was then that Mr. Knight noticed his daughter's state, the bruises on her arms and the puffy cheeks. Something had happened last night.

"What happened?" He simply stated, because he knew that his daughter couldn't and wouldn't lie to him.

"Chuck Bass, he and Blair invited me to that party that you wanted me to go to. Then he took me to the roof and.." Her voice disappeared little by little with each word. Chris, being the one to greet her the night before, had also held her when she had started to cry once again. Chris had gotten the makeup off and helped her into the shower. Then helped her to bed.

"What?! Did he-" Tyler was furious, he looked at Chris with wide eyes but the nanny just placed a soothing hand on his shoulder.

"NO! Dad he just, pushed me against the wall and- and nothing.. he didn't get to do anything before some guy from school then saved me. I think his name is Dan, he punched Chuck in the face" Leo said, happy that something more hadn't happened. She got lucky.

"Good.. good, oh for goodness sake and in a couple of hours we need to go to that stupid brunch" Tyler groaned and stood up from the table, not hungry anymore. Whenever he needed to think her started to pace, or snap his fingers to clear his head.

"Tyler sit your ass down, Leo is a big girl, a strong girl! She will get passed this, now you two are going to get dressed and smile the biggest and fakest smiles in the universe when you attend that brunch" Chris stated, he looked at Leo who smiled back at him. He took her hand and squeezed it tight. Reassuring the girl that she would be alright.

 **~X~**

 **The Bass's Sunday Brunch**

The brunch was in full swing as the Knight family made their entrance. If there's one thing you need to know about Tyler Knight, is that he loves more than anything to spoil his daughter. And there is only one way she would like to be spoiled, which would be jewelry. Sure she had an expensive dress on and killer shoes. But the jewelry around her neck and in her ears made other people gasp in awe.

Take this brunch for example, Chris had chosen a turtleneck, long sleeved, form fitting wine red dress for her to cover up her bruise. But no one was looking at the dress, they were all staring at the necklace full of multicolored gems, from red diamonds to taaffeite to fire opal, hanging around her neck. As well as the large pearl earrings in her ears. Leonora Knight looked like a true masterpiece.

"What do you fancy? I am already full from Chris's cooking" Her father joked and looked down on his daughter. He was a tall man after all, almost 6'4, while Leo came in on a mere 5'5.

"Well I do like the smell of the pastries.." Leo sighed and reached for a plate. She walked away from her father to collect some fruits and other sweets, not really being in a mood for healthy breakfast fish.

"Would you look at that.. The pretty princess cleans up good after a wild night" Leo looked at Blair and rolled her eyes.

"What do you want?" Leo sighed and walked over to an empty table to sit down. Her tone was sharp as a blade, even though she lacked confidence, Leo wanted to protect herself for getting hurt even more. Turning her head to the side, Blair got a good look at the hickeys on her neck, also some of the bruising on her wrists that the sleeves did not cover. Her anger lessened and felt bad.

"I'm sorry for last night. I never thought that Chuck would-"

"But he did, if that guy from our school hadn't literally ripped Chuck from me I don't know what could've happened" Leo said and looked into the brown haired girl's eyes. She saw remorse.

"Just.. stay away from Nate" Blair then said. Getting her mind back on track. She didn't like this girl, this newbie was a threat.

"I have a presentation due in AP History with him. Kinda makes it hard to stay away" Leo rolled her eyes and took a deep breath. She knew that Blair was the embodiment of 'Hell hath no fury, as a woman scorned' but this was getting ridiculous.

"Look Blair, he is your boyfriend. My classmate. Nothing else, I know you don't like me, but trust me on this" Leo said, her voice so strong that Blair actually believed her. It was also evident in the raven haired girl's eyes, they told nothing but the truth. Something that Blair hadn't seen in a long time, not even in her supposed best friend.

"Okay.. I believe you, but if-"

"There is no if. Okay?" Leo said and smiled, Blair stood up from the table and moved away from Leo. She started to mingle and got caught up by several people, even Chuck himself.

"I can't believe that Serena showed up for this brunch, I told her to stay away" Blair scoffed and turned to look at the devil. Dressed to the T, to impress everyone around him. Though he was sporting a black eye.

"You worried about Nate?" He suddenly asked, as if he knew something. Like he was planning something.

"Just a shot in the dark, think you know what you need to do to get his attention" He added and took out a key from his pocket.

"And what's that?" Blair asked, knowing that what Chuck had planned always had some sort of backlash or catch.

"Key to my suite, Nate's heart and your future happiness" He stated and waved the key around, smirking when Blair took it.

"I'm honored to be playing a small role in your deflowering" He said and turned to look out over the room, his gazed every guest like a pawn in a chess game. His eyes landed on Leo, who looked exquisite in her outfit.

"You are disgusting" Blair said and rolled her eyes.

"Yes I am, so why be shy? Just grab Nate and finish this, report back with details" Chuck smirked and moved along. Letting the game play out as planned.

 **~X~**

Leo was just about to go from the party when she spotted the guy from last night, standing alone in the middle of the room.

"Hi.." She said, walking up to him feeling kind of nervous. She had no idea of what she was going to say to him. But the main focus was a 'thank you'.

"Oh hi! Didn't know that you were here" He said, he had one of those nervous, goofy smiles.

She liked that, it made him look innocent in a room full of sharks.

"Well I go to your school, better believe that my father dragged me here" She stated and shrugged her shoulders. Her hair was out and behaved thanks to a ton of hairspray, she would write a letter of apology to the ozone layer later. Nervously she tucked a stray behind her ear.

"Yeah since last night, kinda weird" He sighed and looked around the room. His voice was almost menacing and angry. But Leo when it wasn't directed at her.

"Mhmm.. My name is Leo by the way" She introduced herself.

"Leo? Odd name for a girl" The guy laughed and shook his head.

"It's actually Leonora, but please don't call me that" Leo explained and giggled a bit.

"Leo then.. I'm Dan, Dan Humphrey" He said and extended his hand for her to shake, which she did. They laughed a bit more at the awkward but nice situation they were in.

"Nice to meet you Dan, and thank you for last night" Her voice almost stammered and she cursed herself. She had been so good lately, but going through something like that would leave a scar and Leo had so many already.

"Leonora! We are going now, say goodbye to your friends" Her father said, standing a few meters away holding their coats.

"Alright dad" Leo said and then turned back to Dan.

"Bye then, Dan" She walked backwards until she turned around to walk with her father out of the party.

"Bye" Dan said, knowing that he smiled and waved to no one. Since Leo was already gone.

 **~X~**

What Leo didn't know was that right after she said goodbye, Blair Waldorf waltzed up to Dan and told him everything. Together with Chuck, Serena and Nate. It was all a mess, a soup of drama. Leonora Knight was even in the middle of it all, even if she didn't know it yet and everything was just getting started.


	3. III part I

**A/N: Thank you so much for reading. Hope you enjoy this new chapter. Please review! XO**

 **~X~**

 **"It has been said that time heals all wounds. I do not agree. The wounds remain. In time, the mind, protecting its sanity, covers them with scar tissue, and the pain lessens, but it is never gone."**

 **\- Rose Kennedy**

Tyler Knight, the man that owns the Knight Group, one of the most wealthiest men in the world. He was also one of the happiest. He had it all. He had the money, the house, the cars, the beautiful daughter and the talented sons that would succeed him. He even had love once, true love. It was that kind of love story that would make a great Nicolas Sparks movie.

It all started in Rome, where they first met. It all went so fast. Love at first sight. She danced alone on the empty streets, to the song of her heart. She hummed and mumbled some lyrics in different languages he couldn't understand, she twirled from time to time and sometimes raised her arms like a ballerina. Tyler had been with his father on a business trip, all day, everyday and it had been meetings upon meeting and then more meetings. When he spotted her, he fell. Hard and fast.

He just had to get to know her. He had to figure the mystery ballerina out. Together they had gotten severely drunk on delicious wine and danced all night long. At one point they even danced in the famous Trevi Fountain. They didn't care about anything, not money, not social statues, not time. They could only see each other.

Two months later they married. Six months after that she had became pregnant with twins.

"They are so big" The angel huffed, running her hand over her large bump. Laying on a sunbathing mattress by their pool.

"They are knights, of course they are big" Tyler stated as he put down his book. He took her hand and kissed her knuckles, then her wedding band.

"Then they need knight names"

And so, Lancelot and Percival was born. Though they prefered the names Lance and Percy. Two boys with energy of a thousand. They always smiled, curious about everything in the world around them. Their favourite question was 'Why?'. He couldn't be prouder of them.

Then, a few years later. The angel smiled and happily stated that a mini-angel was on her way. The knights were stoked, wanting their baby sister to be born right then and there. Then they learned that a baby takes time, a lot of time, to be born. Everything seemed so perfect, everyone in Tyler's life were happy, even his parents that had quite a few things to say about their daughter-in-law when they first met her. His life were the epitome of euphoria.

Until it wasn't. Which happens to be the day the mini-angle was born. Because one minute she was there, resting on the bed after a delivery. Then she was gone. While Tyler had been holding Leonora in the nursery, the angel turned into a devil. And left. When Tyler returned to the mother's assigned room, she was no longer there, only the hospital gown and a note laid on the bed. Saying that she was sorry.

Their love had been a true love story worthy of the silver screen. But it had turned into a tragedy. A tragedy no one wanted to talk about anymore.

 **~X~**

 **Chuck's Apartment**

 **Nate**

It was a weekend to remember, at least to him. Ivy League week was over, Nate would be celebrating. Chuck had planned this amazing party that would be epic and it would really help me de-stress from everything in his life. As Nate started to think about school he remembered the history presentation, which had a deadline of next wednesday. Feeling like a jackass, he picked up the phone to call his partner.

"Hello?" She sounded sleepy, or rather exhausted.

"Hi, Leo. It's Nate" He said and looked over his shoulder, Chuck was busy with getting everything started to notice him.

"Oh Nate.. I was just starting on the history presentation" She stated, Nate heard scrambling and shuffling as she probably moved around with her papers.

"Yeah about that, I have a booked weekend you know with the end of Ivy League week"

"So you are forcing me to do all of the work?"

"No! As soon as I can I will be over to help you, but I might be late today"

"Somehow I'm not surprised" And a punch to the gut. Nice finish.

 **~X~**

 **Knight Residence, Upper East Side**

 **Leo**

Leo sighed and threw the Greek Mythology books away from the table. Her eyes were burning even though she had her glasses on, maybe my eyesight was getting worse. Urgh, this weekend couldn't be any worse. Chris had taken this time off to go and visit his family in Vermont, her father was away on business in Italy, she had no friends to call and only boring reality shows were on tv. The only thing left to do was study, which she was almost done with. The only thing left was the history presentation, and with Nate's bail, she was too tired to even start on it.

Why was she even surprised that Nate acted like everyone else surrounding her? Why did she was a raging feeling of disappointment in her gut, when she really should have a feeling of understanding.

Leo thought about Nate, how his smile made butterflies come alive in her stomach and how seemed to be one of the good guys. But he wasn't one of the good guys, he acted like a god in the books splayed out in front of her. He thought he could do whatever he wanted and be okay with it.

No. Leo would not let another snobby classmate walk all over her. If her partner would ignore the assignment, then she would too. She walked up into her room and found her wallet lying around on her vanity. _Why not?_ The devil on her shoulder whispered into her ear. Why not spend the entire day maxing out her credit cards. Leo had never done it before, she didn't like to shop all that much. But to treat herself to a day off from being pushed around sounded perfect.

 **~X~**

An hour later, Leonora Knight was spotted in the high end boutiques of New York. She was a girl on a mission, finding only the most expensive of simple brand clothing she could find and buy them. Black t-shirts and sweaters, jeans and real leather boots. She felt like a queen walking around the streets with all of her shopping bags, she now understood why girls her age did this as a hobby.

She enjoyed this, the glutton inside of her came out and played. And then spotted the store, it was a very expensive store, selling mostly dresses and shoes and jewelry for parties and outings that required you looking your best. Leo simply couldn't resist, the tomboy inside of her had gone away and someone else took over.

"Hello! What can I help you with?" A lady, about 25 years old with dyed, crisp white hair asked her. The lady had spotted Leo walking into the store with over six shopping bags and quickly jumped into seller mode.

"I.. I don't know, I just saw some shoes and stuff in the window" Leo muttered, now realising that this style wasn't her. It was anything but her, this store screamed Blair Waldorf or Serena van der Woodsen.

"Not quite your style?" The woman asked, sensing that Leo was out of her natural element.

"No, not really"

"Then let me show you these" The woman took out a pair of heels. But it wasn't just _any_ pair of heels. Oh no, these were matte black, modest, with a jeweled buckle around the ankle.

"Wow, they are gorgeous" Leo gasped, her eyes getting as wide as saucers when seeing them taken out of the box.

"And hand crafted, each stone is worth a thousand dollars" The woman stated proudly, touching the ankle buckle, skimming her fingers lightly over the glittering gems.

"Can I try them on?" Leo asked, and then blushed as she realised she had no control over her mouth anymore. Those shoes just spoke to her. Sang like sirens, more or less.

"Of course honey" She handed Leo the shoes and winked to her co-workers, she was about to score the priciest shoes in the store to a young girl with unlimited credit cards.

"They fit like a glove" Leo sighed as she looked at herself in the mirror. She felt powerful, like she could do anything in those shoes. No matter the cost, she needed to have them. "I will take them"

"Perfect"

 **Spotted: The pretty princess is finally releasing she have some money at the bank? Or is some drama cooking and ready to be served? I hope I am invited to the dinner party.**

 **You know you love me, XOXO Gossip Girl**

 **~X~**

 **A/N: Sorry for taking so long. I didn't have a plan over where this story were supposed to go. Now I have and I can start writing with confidence again. Thank you all so much for reading, follows, favourites and reviews. They keep me going onward with this.**


	4. III part II

A/N: The episode in general (tv series speaking), has a lot of jump cuts in between character storylines. So for example you would follow the girls during the day, then cut to the guys at night, then back to the girls only five minutes later during the day and so on. I hope that this makes sense since it follows Chuck and Nates' one and they are rather skipping. Anyways, thank you all so much for reading. Hope you enjoy this new chapter. XO

~X~

Central Park

The day after

Leo felt like today the universe was not on her side. Sure, she dressed up nicely and wore her new 'I can conquer the world' shoes, but it didn't feel right. This wasn't her. Her feet ached, the dress was too tight. Her hair had that feeling of having your it up in a ponytail for too long, making your skull hurt. Chris was walking with her, as well as his new boyfriend Nicc (with two c').

Nicc was a trumpet player on Broadway, but he was born in Florida. Leo liked Nicc, even though he was arrogant and often came in the middle of the night to visit Chris. Walking on the marble stone floors in dress shoes making it obvious that the two lovers were about to spend the night together. She didn't mind it, they were happy together and was still in that newlywed phase. Nicc was also nice and he had a good book taste. They once talked for a whole hour straight about the difference between classics and modern classics. Because yes, there is a difference.

"I need coffee" Leo muttered. She was in great need of stopping so that she could rest. She had been walking around like a newbie runway model, or more like bambi on ice, all morning.

"We will get it, go and sit down, honey" Chris said and kissed her temple and then walked hand in hand with Nicc over the street to a Starbucks. Chris wore a navy blue tailored suit, black dress shoes, a midnight blue pocket square and some nice obnoxious sunglasses, the outfit worked so well with his personality and general aura. It screamed 'I'm an important person, look at me' and true to its nature, he made heads turn his way.

"Well, well… look who we have here. A wannabe fashion icon" The one and only Chuck Bass walked up to her. He laughed as he saw her discomfort, which only made her feel worse about her attire. They hadn't spoken at all since the kiss on the lips party.

"Shut up, my feet hurts" Leo mumbled and looked onto the pavement. She didn't want to have this conversation, she had never felt this vulnerable before and it scared her. All she wanted to do was to run home and into her comfort zone again, but she would probably trip if she took one sprinting step in her new heels.

"That's because they aren't used to torture I presume" Chuck said and looked her up and down. Taking her in once more, like shedding new light at an art piece left forgotten in the corner of the exhibit. She was truly gorgeous, not that he would ever admit that in front of her outloud.

"You presume correctly" She sighed and looked up at him from her spot at the bench. Seeing her like this made many questions race through his mind, not many of them was innocent, but they mostly revolved around her well-being.

"Why are you here? All dressed up I mean" He asked and looked over his shoulder, he had lost his best friend to the bohemian, the two of them were now whispering about something.

"Chris is buying coffee across the street with Nicc" Leo said, making Chuck turn back to the naive little goddess on the bench. She probably had no idea that she had the attention of not only him, but all of the guys on the court close to them. But Chuck noticed it all and drank the information in.

"Nicc?" Chuck raised an eyebrow. A new pawn on his board that he didn't know about. Interesting.

"Chris' new boyfriend" Leo confirmed, which was a bit hilarious to be honest. The first time Chuck had gotten information about Chris, the ex fashion scout turned nanny, he had bursted into laughter and called the whole thing bullshit. Who would turn down money and a career for babysitting a snotty child?

"Ah, I liked Ymir, sad what happened" Chuck said and laughed a bit, making Leo smile a bit too.

"You didn't like Ymir, you liked Kristoffer" She said and looked at him, their eyes locked and an odd feeling seemed to gather in Chuck's chest. An uncomfortable warmth, he hated it.

"That's right! Kristoffer, not Ymir" He said and rolled his eyes. Really, who could keep up with Chris' love life. It wasn't interesting nor valuable enough to remember.

"I find it extremely uncomfortable that you know that much about my life and household" Leo stated and smiled a bit more. It was a sunny smile, one that could make you feel good during bad times. One that could terminate demons of ones mind, because it made you forget them for a while. Like a drug, you wanted to see that smile more often.

"More uncomfortable than those sexy shoes?" Chuck teased and focused on her legs, which were exposed in the dress that she was wearing. Making her look like a true model. Too bad she couldn't walk like one though.

"Much more" Leo laughed and rolled her eyes at him.

"Ouch" Chuck pressed his hand over his chest, right over the place his heart was. Strangely enough, it was beating a bit faster than normal and he hadn't even begun to play basketball yet.

"Hey! Leo, didn't see you there" Nate said and looked at her with an unfamiliar hunger in his eyes. He had never seen the innocent brainiac in a sexy dress before, he even grew hot as his eyes went down her slim legs and ended up staring at her shoes.

"Hey Nate" Leo's voice brought him out of his daydreaming state. He looked at her face, she wore no makeup as usual and it was a mundane look for her.

"She hates her shoes" Chuck stated and looked at his best friend, noticing very well the state of him and probably had a few ideas of what was going on inside of Nate's head.

"They are very nice" Nate said and smiled at Leo, who laughed and waved one of her hands in his direction.

"Thank you! See, manners!" Leo said and laughed at Chuck who just rolled his eyes at her antics.

"Sorry pretty princess.. I beg for your forgiveness" Chuck made a grand gesture and bent down on one knee in front of her.

"Stand up you dingus" She muttered, feeling a wave of nervousness hit her as she started to notice the eyes of other people in the park. Staring at the scene Chuck was causing.

"You don't hear many 'dingus' nowadays" Chuck stated and raised his eyebrow at the girl, making a cute giggle escape from her lips.

"Stop teasing her" Nate rolled his eyes at his best friend and passed him the basketball.

"What was that all about? You whispering over there" Chuck asked, nudging Nate to look back to where he stood before with the brown haired guy Leo didn't know.

"Just talking to him about plans of tomorrow.. That's all" Nate shrugged and looked back at Leo, who had a disbelieving look upon her face.

"Aren't you forgetting something?" She said and raised her eyebrow at him. She couldn't believe him at all.

"..." Nate fell silent, waiting for her response.

"The project!" Leo burst out, almost shouting her words to the whole city of New York. "I have done so much already, it's your turn"

"I'm sorry, I will cancel that and come over so that we can finish it" Nate nodded and looked at Chuck who just shrugged. Meaning it was up to him what he wanted to do.

"Thanks" Leo muttered. Just then Chris returned with his new man, holding a steaming to-go cup towards Leo.

"Ooh, look my little genius is a magnet today" Chris gushed and kissed her temple, as if the guys were there.

"Chris!" Leo muttered as she blushed, a notion that was so utterly cute and innocent the guys almost wanted to say 'awe'. She then muttered an inaudible 'thanks' as Chris handed her the hot starbucks cup.

"No problem sweetie, shall we get going?" Chris said and helped her up onto the feet once more.

"Yes" Leo sighed and took a sip of her coffee. "Bye guys" She waved with her one hand before walking of with Chris and Nicc.

"Bye" They said in unison, which creeped them out immensely.

~X~

Knight Residence, Upper East Side

8:07 pm

The night air of Manhattan was chilly and polluted with whispers as always. Leo had switched out of her alter ego clothes and into the ones that she liked. The clothes that were comfortable above all else and made Leo, well, Leo.

"You looked marvelous today, where did you get the clothes from?" Chris asked. They were having dinner on their rooftop balcony, the lights of the city illuminating their faces with rich flavoured salmon on the menu tonight.

"I bought them.. Yesterday. I felt so trapped and just went out shopping" Leo explained and sighed.

"I have taught you well my dear, those clothes were amazing" Chris exclaimed and sipped on his blood red wine.

"I beg to differ, shocking is a better term for them" Tyler Knight said and sat down by the dinner table. Leo looked at her father as his loaded the fish onto his plate, he wasn't supposed to be home today, at least another week would he be in California.

"Why so?" Chris' eyebrows furrowed together and then switched his gaze to the teenage girl.

"The credit card company called and asked if the cards had been stolen, since the activity on them had gone up with 200 %" Tyler chuckled and started to eat. Chris bursted out laughing at his callus ways and sipped more alcohol.

"I'm sorry" Leo muttered, going back into the shell that she recently escaped from.

"Don't be! Did you have fun?" Her father asked and looked upon his darling daughter.

Leonora, she was kind and never asked for anything. It was him who had given her the cards at the same age her older brothers had. She hadn't used them for much, except for books or other typical 'geeky' things.

"I did have fun.. A lot of it" Leo smiled softly and finished her dinner.

"Why are you here dad.. What happened to California?" Leo then asked, looking at Tyler who shrugged.

"I wanted to see you, I missed you. The company is doing great so I canceled the meetings that wasn't critically necessary for me to attend. I will head back there two days for now. So this is like a vacation of sorts" Tyler said and smiled, taking his daughter's hand in his. They were smaller, softer. When he looked at Leo, he didn't see her mother. Leo was an angel through and through according to him, the apple of his eyes.

"That's great!" Leo said and hugged him as best as she could while sitting next to him. "I am pretty tired though, better go to sleep" She said and stood up from the table.

"Good night, angel" Tyler said, watching her go.

~X~

Knight Residence, Upper East Side

The next day

12:03 pm

The doorbell rang right on time. In the livingroom of the penthouse, books and papers and more books were all over the place. Leo was skimming through a rough text that she'd written five minutes ago, checking and double checking for wrong spellings and grammar issues. It was Chris that let the guest in.

"Oh hello, you again" Chris said to the dirty blonde boy. Raising an eyebrow at his uptight and anxious mannerism.

"I-I'm Nate.. Nate Archibald. Here to study with Leo?" Nate stammered for the first time in his life in front of a person he didn't know. Chris let him in and led him to the living room.

"She has been like that for a couple of hours now, good luck" Chris teased and walked into his private quarters, knowing that he wasn't needed any longer.

"Leo? Hello.. Leo!" Nate nudged the girl on the sofa, causing her to shriek and fall of completely. As a reflex she grabbed his arm, making Nate stumble down with her onto the expensive persian carpet.

"Hi" She breathed slowly at their close proximity. Her heart was beating like crazy, her red glasses had fallen down her nose, making her look very awkward in front of the handsome classmate. One more inch and they would be locking lips.

"Hi" Nate said, wishing that he could do just that. Kiss her into oblivion, it was starting to get clearer, the feeling that he harboured for the cute girl with the red glasses. But he couldn't do anything about it. After all, he was still in a relationship. And there was also Serena, which only made his heart more torn and drawn in different directions.

"Umm… You are very, very close" The shy girl whispered, looking into the handsome boy's eyes. She was blushing like a tomato and had no idea what she should do. In realisation, Nate stood up from the ground and helped Leo up as well. Once the awkward moment had passed, they sat down on the couch again, ready to start studying.

"So.. mythology" Nate said, trying to brush away the moment that had just happened in between the two of them. Which was a good thing because Leo was already in full study mode.

"Oh yeah, so I have done this powerpoint presentation of the two general mythologies, in our case that is Greek and Roman. Then I have started to compare those two and also seen what about them is similar, which is a lot since the romans stole almost everything from the greeks" Leo began and showed the things she had been working on, it was a lot, and everything was impressive. Definitely on an A level.

"Wow, you have done this all by yourself?" He said, feeling terrible that he hadn't been there to help her through it all.

"Yeah, I wanted it done so I started without you. Hope that's okay with you" She said and opened up a larger leather inbound edition of the roman gods and heroes.

"It's fine" Nate said and picked up an exact replica, only on that it was on the greek mythology not roman.

~X~

"So.. what did you whisper with that guy about yesterday?" Leo asked, they had been studying for a while now and the curiosity was growing inside of her.

"Huh?" Nate looked up from his books and papers to look into her green doe eyes.

"That guy in the park, you made plans with him.. I'm sorry I ruined them for you" She said and looked away from him. Blushing at how she probably had ruined his night of fun.

"Oh no! Don't feel bad. He invited me to a poker game tonight, but it doesn't matter, this is more important" Nate said and put his hand on her shoulder, trying to convince her that everything was alright.

"Well, maybe we can play later?" Leo suggested and perked up a bit. This seemed to create a spark in Nate's eyes.

"You play poker?" He asked, intrigued to learn something new about her.

"Some, I'm not that good though" That was a lie. She was the best in her family. She just didn't want to say that to anyone, she wasn't confident enough to own up to it.

"That's sounds great" He said, ready to be done with the project so that he could challenge her. One or two hours later, Nate was ready pass out from all of the words he had read and papers he had written.

"And done.. Finally" Leo said, closing down her laptop after saving everything they had done for the night.

"I am so hungry and exhausted, all I have been doing is reading and writing" Nate chuckled and looked over at his study partner.

"I will order some food. Is chinese okay?" She asked and reached for her mobile phone.

"Anything is okay, I'm starving" He said and stood up from the couch he had been sitting on, stretching his limbs and smiling wider when he heard a satisfying clicking sound. Leo hung up the phone after ordering a ton of food, she stood up as well and looked over at Nate who seemed to be studying her.

"So.. you play poker" He said and raised his perfect eyebrow at her. He didn't believe her at all.

"Indeed I do" Leo said and crossed her arms over her chest. She had no idea that Nate could be so smug.

"Do you want to play a game before the food gets here?" He then asked, challenging her to prove herself.

"Sure, I will show you to our game room" Leo said and walked passed him and up the stairs of the penthouse.

"You have a game room?" Nate asked, following close behind her. They walked up to the second floor and into a large hallway. On the walls there were family portraits and art from all over the world. Everything in the apartment had a sense of wealth around it and it didn't seem to fit in with Leo. She was down to earth and neutral in every way, but her home said only money and lavish interior design.

"So this is it" Leo walked to the last door of the hallway, across from the game room was her own bedroom, but Nate didn't need to know that. Opening the door you would enter a large room, about the double size of Chuck's hotel room, with only large windows to the outside skyline of the city. There was also a balcony following the corner of the building, with a large sofa and armchair group surrounding a firepit out on said balcony and double glass door leading out to it.

Inside there was dark wood paneling walls and it had a general old timer bar feeling to it. With stained glass lamps hanging from the high ceiling and a large bar taking up most of the paneled wall side. On the wooden wall was shelves upon shelves of expensive liquor and alcohol, some even in glass cabinets unopened. There was old neon signs up on the walls with text like 'happy hour' and 'screw it, let's do it' and even an old revolver with two 'bang' that switched every few seconds. On the other side of the room there was another large sofa group and a huge flat screen tv with several gaming consoles hooked up to it. In the corner closest to the door there were two circular, red topped poker tables, with custom decks and chips ready to be used. This was basically a man-cave, or man-heaven.

"It is beautiful, you could have a wicked party here" Nate stated with wide eyes. He looked like a kid on christmas or someone who just found a long lost treasure.

"My brothers used to, but since they moved away I mostly use it to play video games or watch movies on that big screen" Leo stated and moved over to one of the tables that had a view of the darkening sky outside.

"I could imagine that, some movie night though" Nate pointed over to the tv but followed her suit anyway.

"I will deal, and be careful, these are very valuable chips" Leo stated and showed off one black and gold 100 dollar chip.

"Oh yeah? How valuable?" Nate asked, seeming skeptical that these play chips was valuable.

"The whole set is about a million dollars. Dad bought them from a friend of his in Singapore" Leo told him, which made Nate almost drop the chip he was currently looking at.

"They look sexy, black and gold" He said and gave the chip back to Leo so that she could prepare the game for them.

"Believe me when I say that you are not the first person to call these sexy" She giggled and started to deal the cards and chips between them. About 20 minutes later they had gone through two rounds already, since it was only the two of them.

"I can't believe that I lost, twice" Nate muttered, more to himself than to the girl across from him.

"Mhmm.. bow down before the queen of royal flushes" Leo sighed and laughed. Suddenly filled with confidence and happiness, she was drunk of her victories.

"I yield before the queen" Nate laughed and raised an eyebrow at his classmate. "But you said that you were bad at this" He accused and pointed a finger at her which only made her laugh more.

"I may have lied" She teased and stood up from the table.

"You may have? You tricked me!" Nate stood up fast and almost jumped her, which caused them to fall back on one of the couched near the huge tv. Having no idea of how to escape his grip, Leo started to squirm under him. Nate laughed and touched her waist, which made her laugh out and squirm even more. The cute girl was very ticklish.

"Stop!" She laughed more uncontrollably as Nate continued to torture her.

"Do you yield?" He taunted her and tickled her into submission.

"Never!" Leo said as he continued. "I don't bow down to losers"

"Oh really" Nate said and raised an eyebrow, he was hot and bothered at this point. This was all too much for him. He subtly reached higher up on her body and Leo suddenly realised that the mood of the game room had turned from competitive to steamy like a sauna. His hands skimmed over her clothed chest and her breath hitched.

They both realised that once more they were only a breath away from doing something stupid and dangerous. They were risking everything if they moved closer, hell they were doing right now. They couldn't deny it, Nate was torn still. But he knew deep down what he wanted. Her, Leo, he wanted her. Just as he was leaning into her more, their foreheads touching and eyes closing. The buzzer from downstairs could be heard through the penthouse. Like a bucket of cold water they pulled apart, with wide eyes they stared at each other.

"That's the food" Leo said, out of breath from their moment.

"I will pay, you just put this stuff away" Nate said and stood up from the couch. He moved out of the room leaving her to clean up their mess on the card table. Just as Leo walked down the stairs towards the living room, she noticed that Nate was having a problem with the food.

"I need your help" He said as the delivery guy just shrugged and looked over at Leo. Nate walked into the living room and opened up her laptop that was still on the coffee table. She payed the food in cash and said goodbye to the delivery man, apologizing for the extra trouble.

"What is it?" She asked as she put down the bags of food onto the table. Nate had a look of anger and confusion written all over his face which made Leo worried sick.

"My account has no money on it" He said and showed her the screen, which showed that indeed he had no money at all on his card that he just tried to pay with.

"What do you mean?" She said and sat down next to him, waiting for an explanation.

"I mean that this account had 200 thousand dollar last time I checked it, and it's all gone"


	5. IV

**A/N: Thank you so much for reading. Hope you enjoy this new chapter. Please review! XO**

 **~X~**

 **"Don't forget that I cannot see myself - that my role is limited to being the one who looks in the mirror."**

 **~ Jacques Rigaut**

Just holding the mask made Leo feel giddy inside. For this one time event, she would be someone else. She would dress up in a real gown and maybe dance with a prince tonight. Not even Chuck Bass himself would be able to recognise her. The mask itself was simple and elegant, silver lace with large rose gold and pearl flowers on both corners of the eyes and a pattern of wines woven into it. It was rather large and would surely hide her identity, also it looked feminine and exquisite.

"Aren't they beautiful?" Chris gushed as he looked over the dresses on the metallic clothing rack. He had chosen every single one personally, because lord knows that Leo herself doesn't know the first thing about fashion. Last time she tried, she felt miserable just being outside.

She remembers that day from just about a week ago. How Chuck had talked to her and it felt normal. Like nothing had happened. Like the things that had been said and done between them had miraculously disappeared into nothingness. It hadn't, she still felt it. That feeling of not being safe around people she should be okay with. He forced himself upon her, but didn't act like it. Leo wondered if he even regretted his choices. Or was it just her not understanding the situation, was it miscommunication? Was it something wrong with what she was wearing? Was she sending him mixed signals? _No, I didn't. But yet I brushed it off like nothing. Like I was okay with it._ She thought to herself.

"What are you thinking about Leo?" Chris asked, seeing her having an inner struggle while skimming her fingers lightly over the delicate mask.

"Just.. If I did something wrong…" Leo muttered and looked at her friend. Because that was the title of his job. Chris wasn't her nanny, nor babysitter or guarddog. He was her friend. Best friend in fact. Since she had been little he had been there for her, no one could ever replace him.

"Oh my little darling, look at me" She did, she looked into his beautiful eyes and felt ten times calmer already. He had that secret power, that not even her father had. Chris could calm her brain down when it was going 100 miles per hour. Taking a deep breath, she sighed and smiled.

"You did nothing wrong. It is not your fault. It was him who went too far. It was him that touched you when you said no. And maybe deep down, you know that he know of his mistakes. But he has to admit it before you can forgive him honey. You deserve to move on from this, and a proper apology from him" Chris said, he brushed her cheek with his thumb in careful circles. It seemed to calm her down when she no longer felt control over herself. She knew Chris was right.

"The dresses really are gorgeous, thank you for picking these out" She quickly switched the subject, as she often did in the occasion of confrontation. When it all became too much she just wanted to let go, to forget. Even though she should not.

"Only the best for my little genius" Chris stated and took out the dress to his right, a sweetheart neckline and a long mermaids skirt all in white.

"What.. am I getting married?" Leo laughed and brushed a treacherous tear that fell down her fair cheek. It wasn't a sad tear, more of a happy one. This moment was perfect. Nothing in the whole entire universe could ruin it.

"You'll never know sweetie, and you are right.. NEXT!" Chris sighed and put the dress back. They tried dresses for about thirty minutes before Leo officially said that everything from fabrics to zippers made her head spin.

"Last one, then we order pizza and forget about this stupid party" Chris stated, he had been saying no to the last five dresses while sitting in a comfortable armchair and sipping champagne. Nothing seemed to be just right, as it always had to be with him. The last dress was an off the shoulder misty blue dress with silver lining embroidery in form of flowers, similar to Leo's mask. It was similar to the last dress she tried on but the thing that made this dress stand out was the tea length of it. As Leo dressed herself they both knew. This was the one.

"Oh my gosh! This is it! That is the one.. Oh honey you look like a real queen!" Chris exclaimed and hugged Leo, who just laughed at her friend's behaviour. She took a light spin in it, loving how it flared a bit around her.

"Thank you, I adore it" Leo said and giggled, spinning one more time before going behind the extravagant silk and cherry tree dressing shade to switch into something more comfortable.

"Me too, now get out of it while I order some pizza" As instructed, Leo did. Later on, when dressed in grey sweatpants and a black The beatles sweatshirt, she was going down the staircase towards the kitchen when her phone buzzed.

 _Prince Charming : Could use a friend atm, can I come over?_

 _Leo : Sure thing, we are ordering pizza._

15 minutes later, both Nate Archibald and three pepperoni pizza's entered the front door.

"We got one for you honey, I will leave you kids alone. My soap opera is on" Chris exclaimed and moved to his own living quarters, which was like an apartment inside of the penthouse. Leo herself had never been inside of it, but the man had often gushed to her father about how lavish and extraordinary designed it was.

"Thanks Chris" Nate had met Chris two times before, once in central park and the other when they had studied together. His first impression was wonder of how much of a loving parent he was towards Leo.

"So, what's up?" Leo asked, looking at Nate with furrowed eyebrows. The past week they had grown closer due to many factors, but also because they ace'd the history project presentation.

"My dad.. He is doing drugs" Nate blurted out, his facial expression changed like a ton of brick had disappeared off his shoulders. Relief and confusion was all that was left of him.

"What?" Leo whispered, afraid of the rest of the world listening in on them.

"I found coke in one of his books the other day.." Nate began but Leo just stood up from the dinner table, interrupting him.

"That is.. Oh my-"

"Please don't freak out, okay.. Leo you need to be my rock right now" Nate moved away from the table to stand across from her. Her gaze was on her hands as a million thoughts ran through her brain. She needed to remember how to breathe properly, in and out.. In and out.

"Of course I will you dingus! Just, this is all very hard to smelt in" She sighed and closed her eyes, her head fell against his chest. Nate didn't move an inch, her being this close to him felt nice. Like their time together before. It always seemed to feel, right, between them.

"I know" He said and put his arms around her carefully. She didn't wince or move away, which was a good sign.

"Can it be old stuff, you know leftovers from the 90's or something. People did way worse stuff back then, compared to what teenagers do now" She argued, trying to make sense of the situation.

"It isn't old, and it makes total sense. He said he had some money problems" Nate said, thinking back on his own previous theories. With his bank account suddenly drained and then filled up again as if it was just a common mistake. Since when is it a common mistake to move around 200 thousand dollars?

"Have you asked him about it?" She whispered and hugged him tighter, all of this drama made her feel bad for him.

"Yeah.. I just wish, you know, that he would be honest with me. Like he and my mom made some secret pact to act like robots" His laughter was cruel and unforgiving. Like he had have enough of bullshit in his life.

"But that is the way that our kind of parents are.. Nate, if your dad is doing what you are telling me. Then he is probably really scared and if you want to connect and get him to talk you have to tell him how you really feel" She said, trying to to sound strong for him.

"Don't give up" Leo added, taking his hand in her much smaller one.

"You get me, it is a refreshing feeling" He said, moving his hand so that he could lace his fingers through hers,

"No problem, I will always be here for you Nate.." She stated, not pulling her hand away.

 **~X~**

"Leonora Knight" She said to the bouncer, the man nodded and made her move along into the party. This was the second time she was going out to party, crossing her fingers, she hoped that this night would be way better than the last one.

She moved around the place. Smiling at people who said hi to her, believing she was someone else, and also guys that complemented her as she walked passed. No one knew her and it was amazing.

What was also amazing was the venue. Leo had never seen anything quite like this before, straight out of a fairytale ballroom. Yet more mysterious and sensual. She easily spotted Blair with her trio of friends. Chuck and Serena was with her too. At least Leo thought it was them, but their back was turned to her so she wasn't sure.

"Dan!" Leo exclaimed, easily spotting his even with his mask on.

"Hello?" He said, not really sure who he was talking too. But he seemed to remember the sweet voice of the girl coming towards him.

"It's Leo" She stated and laughed at his revelation. His face looked funny with his eyebrows raised.

"Oh my- Leo! You look amazing.. I didn't recognise you" He said and looked at her up and down. She truly was a sight to behold with her dark dress and silver mask. Her black hair was up in a fancy bun and she wore some dark makeup on her.

"Well job well done then" She smiled widely and twirled around before him.

"So how are you?" He said when the girl slowed down to look at him again.

"I'm better, time heal wounds.. Slowly but surely" She reassured him. Being at this party was a step forward. She was growing up after all, and slowly breaking out of her shell.

"That's good" He nodded and looked around the venue, to see if he could spot Serena nearby them.

"And how are you?" She asked, smiling at how nervous he looked.

"I'm great, I will be looking for Serena.. So golden hair you know?" He sighed and looked around once more, seeing several girls with that haircolor.

"I think I spotted her in a yellow dress. But my eyes may be deceiving me. Since I have contact lenses on for the first time in forever" Leo stated and pointed in the direction of Serena Van der Woodsen.

"Thank you.. And talk to you later?" He said and started to walk away from her.

"Sure, bye" She muttered, kind of sad of his early departure. She looked around the room to see if she could spot Nate. Maybe she would muster up the courage to ask for a dance with him. Nothing romantic about it, just a friendly 'I may have a crush on you' dance. Couldn't be that hard… right?

"Found you" A voice said behind her, which made her soul briefly jump out of her mortal coil. She turned around and faced the man in the red suit.

"Dammit" She muttered and rolled her eyes, which kind of hurt because of her contact lenses. Maybe they wasn't on properly.

"Don't look so surprised.. But I need to talk to you" He said and motioned over to a hallway away from the party.

"No way, I am waiting for someone actually-" Leo turned around to seeing none other than Nate Archibald. Kissing a blonde girl in a yellow dress. _Serena_ , She thought and suddenly wanted to cry. It felt like a blow to her stomach and reluctantly she turned back to the devil.

"You were saying?" Chuck raised an eyebrow at his friends antics. But would use it against him later. Now he had more pressing matters at hand.

"Five minutes" She muttered and followed him away from the party once more.

"In here" He said and opened a dark door, that lead into a dark room.

 **~X~**

It was a room with fairy light hanging from the celing and dark silks on the walls like the rest of the party place. Obviously this was a secret room meant for a couple to get some privacy when dancing, or doing other things. There was also a door in the left corner that probably lead outside with a sign saying that it was only used for personnel in the building.

"Chuck, how did you know?" Leo asked, she felt exposed and like a deer caught in a hunter's trap. This wasn't how her magical night was supposed to go. Once again everything was ruined because of _him_.

"Know what?" Chuck said and took of his devil's mask. Funny enough he still remained the devil.

"That it was me in this get up?" She said and tried not to look at him. Her thoughts went back to their earlier conversations and how easily it was to forget some things that almost happened. Maybe she wanted to forget, as a defensive act to protect her mind from over analysing and going through that moment over and over again. Maybe she just wanted it all to be over and move on. But she couldn't, ironically enough, it was her heart that shouted stop loud and clear. The same naive little heart that had been crushed moments ago. Now it wanted revenge.

"You can never hide from me Leonora.. Don't you see it? You are way too beautiful, even when you try to hide behind your mask" He said, Chuck gestured a lot with his hands. Out of control over his own frustrated body. He didn't know how to act, how to behave. How to beg for something. Something as important as forgiveness. He had never done it before because he lacked shame. But now he felt it, it filled him to the brim. Shame and more endless shame.

"Are you going to hurt me?" She whispered as he came closer to her, because he needed to be sincere and close and he couldn't do it from across the dark room.

"Never" He said back, his voice low and full of sadness and truth.

"Liar-" He almost had her fooled. She had endured torture from this guy for years, he had put her through hell. Now she knew how to fight for herself, but before she didn't. She submitted to forgive and forget. Bury and never to be spoken about again. Because that is what happens on Upper East Side. Even if she would've reported it, it was just almost rape. His father would've paid the amount of money their lawyers agreed upon and then it would be yesterdays news. Nothing to remember.

"Last time we talked as if nothing had happened" He said, once again trying to break down the walls she had put up around herself to keep him and other people out. They had been playing the game for too long. For too long had they moved strategically, neither of them getting a checkmate. Leo was done with this. The board was filled with moves from both sides, hurting each other to no end. He attacked, she defended. For years. But he had gone too far. He had taken the game too seriously.

"But something did happened.. I was stupid to blindly talk to someone like you like a normal person" After everything he'd done. She still felt the hope there in her belly and her naive heart. The hope that he could change. But it was a false hope, her brain knew that much.

"Like me?" He chuckled, they were still so close to each other. He was taller than her, he easily overpowered her. Why did the devil alway portray himself as a handsome man? It was ridiculous.

"Someone that acts good towards the right people.. When in truth you are a devil, I have seen both sides of you" She whispered, she didn't want to cry. But she was weak. She wanted to leave this party, this conversation, this life. She wanted to be gone from the Upper East Side.

"I regret everything" He stated, with such force she almost believed him. She almost believed the pathological liar.

"It's too late for that Chuck.. You tried to rape me" She muttered and finally turning away from him. She turned her back to him. She had decided to walk away. One step at the time she walked to the metal door leading to her freedom.

"It's more complicated than that" He said and took her hand. Not forearm nor shoulder. Not roughly either. He took her hand to lead her back to him. The act made her feel strange, it wasn't invasive and extremely uncomfortable, more begging and gentle.

"What? Tell me! How can it be more than that simple thing.." She whisper shouted. No longer caring about her tears. This was all too much, Nate kissing that blonde, Chuck begging for forgiveness.

"You are too good!" He stated, his voice rough with emotion. _Lies.. only more lies. Stop listening, run._ She thought inside of her head. More like a chant to herself.

"Urgh Chuck! We have been through this already.. I don't get it" She said and turned to walk one more step. But he didn't let her.

"You are too good for me.. But I want you.." He was right behind her. Still holding onto her hand like a lifeline. He spoke in his rough, lying, percussive voice.

"Chuck-"

"Please.. Forgive me" He begged. He was at a loss though.

"How?"

"Give me a chance to prove that what I mean is true-"

"But all you do is lie, Chuck" She said and took another step. This time she broke free from his grip on her hand. She was finally free.

"I know" He said, his voice getting more quiet as she walked towards the door.

"And you deceive, and you hurt people and you do it for fun-" She said, stopping to look over her shoulder. She was defeating her demons tonight.

"I know"

"I can't Chuck" She shook her head and opened the door, the cold air from the streets made her smile and breathe in and out slowly.

"I will prove myself to you.. That I am sorry, hopefully you will see that someday" He said and smiled his crooked, wicked smile. She didn't know his motives anymore, but no longer could he hurt her. The night was over and so was the battle between them. The board was swept clean, and the only pieces on the new one was the two of them.

"Goodbye Chuck" She said and made her first move. Away from him.

 **~X~**

 **A/N: When I wrote this chapter I listened to two songs. Woman and Praying by Kesha. Such amazing songs really fueled me to write this. And it all came out so easily.**

 **As a reviewer said, it is strange that Chuck and Leo could talk so casually with each other in chapter 4 (III part II). I wrote that in the previous chapter for a reason. To rebuild something just must tear down the old thing. And that conversation, where the two of them seemingly talk to each other as if nothing had happened was the set-up for this event.**

 **To forgive someone is hard, especially when you have history with them. And even if you forgive you never forget it. It will be a slow burn between them, but they took a step forward and talked about it. Hopefully you readers like what I have in store, please review your thoughts and emotions. XO**


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